I Will Never Forget

Here’s wishing everybody a fantastic weekend on this first one of December. The cold is here, the sun has gone and columns await in the lab. Of which I have been doing my up-most best to avoid in favour of recrystallizations but with no luck at all. So Friday I bit the bullet and got columning. It revealed my crude had waaaaaaaay more crap in it then I initially thought and explained why a recrys was probably never going to happen. The only thing to lift my mood was the choice of vanillin TLC stain. Smells like Christmas and is perfect for when those UV lamps are playing up. 6 g of Vanillin and add 100 ml ethanol. After this, add 1.5 ml of Conc. H2SO4 to give a colourless solution. This will turn yellow after a few TLC plate dips and that’s perfectly OK. Take care not to overdo it with the heat gun…

Vanillin: The smell of Xmas.

More presentations this week where I did my best to keep at a reduced pace and not to rush off too much. When discussing the chemical modification of proteins with organic chemists you have to be very patient as it’s not the usual chemistry they are familiar with. Hell it’s not even chemistry I would say I am familiar with and it’s my project! I went with the tag line “And Now for Something Completely Different” as it certainly sets the tone for the rest of the ride. Gone is the ability to play with solvents and mad temperature and pH ranges. Gone is traditional protection group chemistry. The tool box is still being written and all reactions have to adhere to the rules of proteins, strictly physiological conditions. 37°C, water, neutral pH as well as not interfere with all the other functional groups kicking around. And after all this, the modified protein must retain its function. A review on this area that is beautifully written albeit a little dated now is titled “Fishing for Selectivity in a Sea of Functionality”. Couldn’t have worded it better myself. I feel I delivered it well and it went much better than my previous attempt which I wrote about here a couple of blog posts ago.
This week’s #ReactionRecap we are going to look over the Heck reaction. 2010 Nobel prize winner Richard Heck developed this palladium catalysed C-C coupling of aryl halides (or alkyl halides) with activated alkenes. Heck’s work without question facilitated the rise of palladium catalysed coupling reactions, most notably the Suzuki reaction and Negishi coupling.
This mechanism follows a classic Pd catalytic cycle of oxidative addition, insertion followed by a reductive elimination to kick out the product and regenerate the Pd catalyst.
Heck’s palladium work is extremely scalable and used in the commercial synthesis of the anti-inflammatory drug Neproxen as well as the asthma drug Montelukast.


A basic Pd catalysed Heck reaction


Finally, I have one more thing I wish to get off my chest. I found out over the weekend that I’d lost an old school friend. James ‘Bobby’ Robinson. I have made no real post on social media about this because in all honesty I’m not sure I have the words. Even now nearly a week on it’s still not really sunk in. My heart goes out to his family in this time of sadness.
In truth I hadn’t spoken to Bobby in a while. Longer than I would wish to admit. I suppose even in 2016 when it’s basically impossible not to lose contact with someone we still found our paths going very different ways.
We were in practically every class together growing up for 5 years. Sadly, I have probably forgot the majority of the laughs we shared over that time. But there are some things I will never forget.
I will never forget the way every drama lesson we had turned into an organised fight. The slap that was heard around the world and that infamous chair bump. Ms Byrn probably fucking hated us. I will never forget creative writing in English and you in auto-pilot mode writing out shit I was saying to you aloud. The look of horror on your face when you realised you had half a paragraph of transcribing my convo with you. You probably had to be there I guess but we were chuckling like school girls over it. I will never forget that Rugby match when we weren’t allowed on the same team together. Normally when it snows you’re supposed to go inside but that was never going to happen with that psycho PE teacher (Forget his name; Bold guy with massive calves) It swiftly descended into a “who can tank the each other hardest”. We came out of that that thing bruised and battered and it was fun as hell. I will never forget our geography lessons spent seeing who could wind up Mr Chidziya the most. God I was howling at the amount of detentions that were threatened but never delivered. There are plenty more I could list. I will never forget French and those damn snake toy things keeping us occupied because fuck learning French. The one worth mentioning the most was maths with Mr. King. I will never forget. We were on the top floor in some forgotten room in East block. Mr. King had long since stopped caring about the lessons or us. In fact, now I come to think of it he had left us all together and it was substitute after substitute after substitute. “Gooch can I borrow your book”. Now why on earth you wanted my book I didn’t know. Firstly, there was nothing in it because no way I’m doing shit set by substitutes week in week out and secondly, and more importantly, you were far better at maths than I. Always were. So I hand over my mostly empty book and …. Ciao work book. You launched that bitch out of that top floor window and god damn did it fly. I couldn’t stop laughing. Neither of us could. Thinking about it now cracks me up still.
Then some 3 weeks later when things had moved on we go back to that forgotten room in East block for yet another maths class and low and behold there was no substitute. Mr King had returned, our glorious leader. Back with a vengeance. We sat down realising the gig was up and we’d probably have to actually do some work from now on. When everyone had filed in and the dust had settled, without uttering a word he walked over to our desk and produced a beaten and sad looking maths book out where on the front next to the name it had “Gooch”.
“Ah cheers sir… Wondered where I’d left that”
“Don’t misplace it again…”
We gave each other a sideways glance and had to fight the laughter back again.
So here’s to you Bobby. Thank you for some of the best memories growing up and a true friend all round. I am sad you are no longer here. Really sad. But I’m doing my best to focus on the joy you brought every day and encourage others to do the same. I miss you and I’m sorry we are where we are. Go easy bro.



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